CN1643077A - Azo dyes - Google Patents
Azo dyes Download PDFInfo
- Publication number
- CN1643077A CN1643077A CNA038066084A CN03806608A CN1643077A CN 1643077 A CN1643077 A CN 1643077A CN A038066084 A CNA038066084 A CN A038066084A CN 03806608 A CN03806608 A CN 03806608A CN 1643077 A CN1643077 A CN 1643077A
- Authority
- CN
- China
- Prior art keywords
- formula
- azoic dyestuff
- choh
- con
- dyestuff
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000987 azo dye Substances 0.000 title abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 19
- 239000004033 plastic Substances 0.000 claims abstract description 12
- 229920003023 plastic Polymers 0.000 claims abstract description 12
- 239000002245 particle Substances 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000460 chlorine Chemical group 0.000 claims abstract description 6
- 229910052801 chlorine Chemical group 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 239000000975 dye Substances 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 13
- 239000000049 pigment Substances 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- 230000019612 pigmentation Effects 0.000 claims description 10
- 238000005859 coupling reaction Methods 0.000 claims description 8
- 239000011368 organic material Substances 0.000 claims description 8
- 230000008878 coupling Effects 0.000 claims description 7
- 238000010168 coupling process Methods 0.000 claims description 7
- 238000006193 diazotization reaction Methods 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 238000006068 polycondensation reaction Methods 0.000 claims description 3
- 238000012644 addition polymerization Methods 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 11
- -1 (methyl) acryl group Chemical group 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 239000003643 water by type Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 230000000176 photostabilization Effects 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 3
- 239000004902 Softening Agent Substances 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000011260 aqueous acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002932 luster Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920006222 acrylic ester polymer Polymers 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 229960002719 buserelin Drugs 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000549 coloured material Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
- 239000011049 pearl Substances 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
- C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
- C09B29/3639—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more amino groups
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Polymerisation Methods In General (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Photoreceptors In Electrophotography (AREA)
- Coloring (AREA)
Abstract
The present invention relates to an azo dye of formula (I) wherein R1 and R2 are each independently of the other -NH-(CH2CH2)-OH, -NH-CH2-CHOH-CH2-OH, -NH-(CH2CH2)-S-(CH2CH2)-OH, -NH-(CH2CH2)-NH-(CH2CH2)-OH, NH-CH2CH2-CON(CH2CH2OH)2, R3 is -CN or -CONH2, R4 is methyl or trifluoromethyl, R5 is -CF3, -COOC2H5, R6 is hydrogen or chlorine and R7 is hydrogen, chlorine, bromine or -NO2, to a process for the preparation thereof and to the use thereof in a method of producing mass-coloured plastics or polymeric colour particles.
Description
The present invention relates to novel azoic dyestuff, its preparation method and its produce mass pigmentation plastics or polymkeric substance pigment particle and to semi-synthetic or the synthetic hydrophobic fiber material is painted or method of printing in purposes.
The dyestuff that is used for the mass pigmentation plastics is known.For example, in United States Patent (USP) 5367039, described and had 1,4,5 of (methyl) acryl group, the quaternary anthraquinone of 8-, this compound can with the vinyl monomer copolymerization, therefore be applicable to and produce painted vinyl polymer.
Yet up to now, the dyestuff of use still can not satisfy photostabilization and the particularly peak demand of thermostability aspect.Therefore, need novel heat-staple dyestuff, this dyestuff can generate to have high tinctorial strength and demonstrates photostabilization, particularly high temperature photostabilization, and the color and luster with good Synthesis durability.
United States Patent (USP) 3998802 discloses 2, and 6-diamino-pyridine based azo dyes, this azoic dyestuff are applicable to according to dying synthetic polymeric amide and polyester to the greatest extent painted, and famous with good weather resistance for thermal-setting and light.
Surprisingly, have been found that now, specific 2,6-diamino-pyridine based azo dyes is suitable for synthetic polymer is carried out mass pigmentation, obtains having high tinctorial strength, demonstrates photostabilization, special high temperature photostabilization and color and luster with good Synthesis durability.
The present invention relates to the azoic dyestuff of formula (I):
Wherein:
R
1And R
2Be independently of one another separately-NH-(CH
2CH
2)-OH ,-NH-CH
2-CHOH-CH
2-OH ,-NH-(CH
2CH
2)-S-(CH
2CH
2)-OH ,-NH-(CH
2CH
2)-NH-(CH
2CH
2)-OH ,-NH-(CH
2CH
2)-NH
2,-NH-CH
2-CHOH-CH
2-NH
2,-NH-CH
2-CON (CH
2CH
2OH)
2,-NH-CH
2CH
2-CON (CH
2CH
2OH)
2,
Or
R
3Be-CN or-CONH
2,
R
4Be methyl or trifluoromethyl,
R
5Be-CF
3,-COOC
2H
5,
R
6Be hydrogen or chlorine and
R
7Be hydrogen, chlorine, bromine or-NO
2
Substituent R
1And R
2Can be identical or different, preferred, R
1And R
2Identical.
Preferred R wherein
3Be-CN R
4It is the azoic dyestuff of the formula (I) of methyl.
Preferred R wherein also
1And R
2Be-NH-(CH
2CH
2)-OH or
The azoic dyestuff of formula (I).
In addition, preferred R wherein
7It is the azoic dyestuff of the formula (I) of hydrogen.
In formula (I), R
6Be preferably hydrogen.
The azoic dyestuff of particularly preferred formula (I) is compound (Ia), (Ib), and (Ic) and (Id):
The compound of formula (I) can for example prepare by the diazotization of aromatic amine and coupled reaction subsequently according to known method preparation.
The present invention also relates to the preparation method of formula (I) azoic dyestuff, it comprises according to the method for the routine compound diazotization with formula (II):
Wherein, R
5, R
6And R
7Define as above, and then make the coupling component coupling of diazotizing compound and formula (III):
Wherein, R
1, R
2, R
3And R
4Definition as above.
The diazotization of formula (II) compound is carried out in a manner known way, for example at the aqueous acid medium, uses Sodium Nitrite to carry out in aqueous salt acid medium or the sulfuric acid medium.But, also can use other diazo reagent, carry out diazotization as nitrosyl sulphuric acid.In diazo process, can there be extra acid in the reaction medium, for example the mixture of phosphoric acid, sulfuric acid, acetate, propionic acid, hydrochloric acid or this class acid, for example mixture of propionic acid and acetate.Advantageously, diazotization is at-10 to+30 ℃, and for example 0 ℃ is carried out under the temperature of room temperature.
Coupling between the coupling component of the diazotizing compound of formula (II) and formula (III) is equally also carried out in known manner, for example in aqueous acid medium or water-based organic medium, advantageously at-10 to 30 ℃, particularly is lower than under 10 ℃ the temperature and carries out.The acid of using can be, for example hydrochloric acid, acetate, propionic acid, sulfuric acid or phosphoric acid.
The compound of formula (II) is known or can prepares with known mode itself.
The coupling component of formula (III) is known equally or can prepares with known mode itself, for example by making 2 of formula (IV), 6-dichloropyridine derivative and suitable amine prepared in reaction.
The present invention also relates to make the method for mass pigmentation plastics or polymkeric substance pigment particle, it comprises the azoic dyestuff of high molecular weight organic materials with at least a formula (I) of painted significant quantity is mixed.
The azoic dyestuff of use formula (I) carries out painted for example by using roller mill, mixing tank or grinding tool to carry out to high-molecular-weight organic material matter, so that this dyestuff mixes with this base material, described dyestuff dissolves or is finely dispersed in the high molecular weight material.Then, pair process with dyestuff blended high molecular weight organic materials according to known method itself, for example, use calendering, pressing mold, extrude, apply, rotate, pour into or injection moulding, the result is the coloured material that has obtained final form.The mixing of dyestuff can also be carried out before the procedure of processing that will carry out reality at once, for example the composition by simultaneously directly solid-state for example powder dye and granular or powdered high molecular weight organic materials and (when suitable words) being also had other continuously for example additive be fed to together in the intake zone of extrusion machine, these components just mixed before processed.Yet, generally, preferably in advance dyestuff is blended in the high molecular weight organic materials, because can obtain more even painted base material like this.
For the goods of making non-rigid shape or reduce its friability, often wish before moulding, so-called softening agent to be incorporated in the high-molecular weight compounds.Can be used as having of softening agent, for example, the ester of phosphoric acid, phthalic acid or sebacic acid.In the method for the invention, softening agent can be incorporated in the polymkeric substance before or after adding tinting material.In order to obtain different tones (colour shade), except that the azoic dyestuff of formula (I), also can join other pigment or other tinting material amount in the high-molecular-weight organic material matter optional other additive, for example filler or the siccative of also adding with hope.
Preferably the thermoplastics that thermoplastics particularly is fibers form carries out painted.Can be according to the present invention painted preferred high molecular weight organic materials be the polymkeric substance of very usual specific inductivity 〉=2.5, polyester particularly, polycarbonate (PC), polystyrene (PS), polymethylmethacrylate (PMMA), polymeric amide, polyethylene, polypropylene, styrene/acrylonitrile (SAN) or acrylonitrile/butadiene/styrene (ABS).Special preferred polyester and polymeric amide.More particularly preferably be the line style aromatic polyester, it can be by terephthalic acid and glycol, particularly the polycondensation of ethylene glycol obtains, or terephthalic acid and 1,4-two (methylol) hexanaphthene and condensation product, for example polyethylene terephthalate (PET) or polybutylene terephthalate (PBT); Also have polycarbonate, for example by α, alpha-alpha-dimethyl-4, those that 4-dihydroxyl-ditane photoreactive gas obtains are polymer based with polyvinyl chloride and polymeric amide perhaps, for example polyamide 6 or polyamide 6 .6.
Because the compound of formula of the present invention (I) comprises at least 4 active H atoms (being respectively NH and OH group), therefore, dyestuff can be mixed with monomer and its form with comonomer is introduced directly in the polymer backbone, condition is that monomer includes the active hydrogen atom reactive activity group with NH, OH or SH group.This monomeric example comprises epoxide (Resins, epoxy), isocyanic ester (urethane) and acyl chlorides (polymeric amide, polyester).
Therefore, the invention still further relates to the method for making mass pigmentation plastics or polymkeric substance pigment particle, it comprises making and comprises that at least a monomeric mixture that includes at least one NH-or OH-active group and can carry out polymerization, addition polymerization or polycondensation and the compound of at least a formula (I) react.
The invention still further relates to the purposes of compound in producing mass pigmentation plastics or polymkeric substance pigment particle of formula (I), and painted plastics and the polymkeric substance pigment particle of the compound of use formula (I).
Dyestuff of the present invention makes above material, particularly polyester material have all flat tone (level colour shade) of high tinctorial strength, and this tone has good useful life longevity, particularly good high temperature photostabilization.
Dyestuff of the present invention can also use with other dyestuff at an easy rate and form the miscellaneous tone.
In addition, dyestuff of the present invention can also be used for the coating occasion of any kind of.
In addition, the azoic dyestuff of formula of the present invention (I) also is suitable for being used to produce colour filter as tinting material, especially for the colour filter of 400-700 nanometer visible light, is used for the colour filter of liquid-crystal display (LCD) or combination of charge element (CCD).
By continuously redness, blueness and green colourant being applied to suitable base material, for example produce the method for colour filter on the amorphous silicon referring to GB-A-2182165.Colour filter can for example pass through, use contains the printing ink of azoic dyestuff of the present invention, particularly printing-ink is coated with, and perhaps can for example prepare by azoic dyestuff of the present invention is mixed with available chemistry, heat or the structurized high molecular weight material of photodissociation mode.Other manufacture method can for example be similar to EP-A654711, by being administered to base material for example on the LCD, carrying out photo structureization then and develops and carry out.Other document of describing colour filter production comprises US-A-5624467, Displays, 14/2,115 (1993) and WO98/45756.
Use the difference of the colour filter that is used for liquid-crystal display (LCD) of azoic dyestuff of the present invention preparation and other colour filters to be the high-transmittance of color dot.
The invention still further relates to azoic dyestuff of the present invention as the purposes of tinting material in producing colour filter.
Following examples are used to illustrate the present invention.
I. prepare embodiment
I.1 the compound of formula (1a)
A.2,6-two (2-hydroxyethylamino)-3-cyano group-4-picoline is synthetic
With 1075 milliliters of thanomins at room temperature (RT) be incorporated in the Florence flask.Use powder funnel, in 30 minutes, import 472.3 grams 2,6-two chloro-3-cyano group-4-picolines.Use water-bath that thermopositive reaction is cooled off.Product dissolves fast, and thermopositive reaction calms down.After 30 minutes, internal temperature is 30 ℃, adds 100 milliliters of thanomins in addition again.Simultaneously solution was being stirred 10 minutes in addition with the water-bath refrigerative, postheating is 115 ℃ to internal temperature.After 20 minutes, internal temperature reaches 135 ℃, uses water-bath that flask is cooled off again.Reaction mixture is stayed standing over night under the room temperature, then 115 ℃ of restir 4 hours.Under the ice bath cooling, subsequently reaction soln is poured in the hydrochloric acid of 5 liters of 1N; Form precipitation soon.The hydrochloric acid that adds 1 liter of 1N, and, make its internal temperature rise to room temperature light brown suspension stirring 2 hours.Leach precipitation, with the hydrochloric acid of 1 liter of 1N and the washing of 10 premium on currency, subsequently 50 ℃ in vacuum drying chamber dry 2 days.Yield: 551.8g (93.4%)
B. use 2-ADP base sulfone diazotization
14.7 gram 2-ADP base sulfones are suspended in 160 milliliters of Glacial acetic acid.Add 18 down at 15-18 ℃ then and restrain 32% hydrochloric acid, and drip the sodium nitrite solution of 15.3 milliliters of 4N.After 15-18 ℃ is stirred 1 hour, destroy excessive nitrite by adding 10% thionamic acid.14.5 grams 2,6-two (2-hydroxyethylamino)-3-cyano group-4-picoline is incorporated in 250 ml waters.Dropwise 5 drips 2,4,7, and 9-tetramethyl--5-decine-4 after the hydrochloric acid of 7-two pure and mild 10 grams 32%, is cooled to 15 ℃ with solution, adds the solution and 100 ml waters of 50 gram ice, 2-ADP base sulfone diazonium salt afterwards.Reaction mixture stirred 1 hour, and then added 200 ml waters.Leach precipitation, washing is also dry.Yield: 29.1g (100%)
I.2 the compound of formula (1b)
7.5 gram 2-amino phenyl sulfonyl acid phenenyl esters are dissolved in 80 milliliters of Glacial acetic acid.Subsequently, under 15-20 ℃, drip the hydrochloric acid of 8 grams 32% and the sodium nitrite solution of 7.6 milliliters of 4N.After 15-20 ℃ is stirred 1 hour, destroy excessive nitrite by adding 10% thionamic acid.7.1 grams 2,6-two (2-hydroxyethylamino)-3-cyano group-4-picoline is incorporated in 100 ml waters.Drip 22,4,7,9-tetramethyl--5-decine-4 after the hydrochloric acid of 7-two pure and mild 5 grams 32%, is cooled to 15 ℃ with solution.Then at 15-20 ℃ of solution that adds down 2-amino phenyl sulfonyl acid phenenyl ester diazonium salt, suspension stirred 1 hour under the refrigerative situation not carrying out, and added 50 ml waters then.Leach precipitation, washing is also dry.Yield: 14.2g (96%)
I.3 the compound of formula (Ic)
11.6 gram 2-aniline sulfonic acid N-phenyl-N-buserelins are dissolved in 100 milliliters of Glacial acetic acid.Subsequently, drip the hydrochloric acid of 14 grams 32% and at 15-20 ℃ of sodium nitrite solution that drips 10 milliliters of 4N down.After 15-20 ℃ is stirred 1 hour, destroy excessive nitrite by adding 10% thionamic acid.9.9 grams 2,6-two (2-hydroxyethylamino)-3-cyano group-4-picoline is incorporated in 160 ml waters.Dropwise 5 drips 2,4,7, and 9-tetramethyl--5-decine-4 after the hydrochloric acid of 7-two pure and mild 6.6 grams 32%, adds 50 gram ice.Afterwards at 15-20 ℃ of solution that drips 2-aniline sulfonic acid N-phenyl-N-buserelin diazonium salt down.Suspension stirred 1 hour not carrying out under the refrigerative situation, added 100 ml waters then.Leach precipitation, washing, drying, and use ethyl alcohol recrystallization.Yield: 18.2g (87%)
II. Application Example
II.1. make the colour filter that is used for liquid-crystal display (LCD)
Comprise 83.3 at 100 milliliters and restrain in the Glass Containers of zircon porcelain pearls, use azoic dyestuffs, the 0.28 gram Solsperse of Dispermat 2.8 gram example I .1
_5000,4.10 gram Disperbyk
_161 (dispersion agents, wherein comprise the solution that pigment is had 30% concentration that the high molecular weight block copolymer of the group of affinity forms in n-butyl acetate/acetate 1-methoxyl group-2-propyl diester of 1: 6, BYK Chemie) and 14.62 gram acetate 1-methoxyl group-2-propyl diesters (MPA) under 23 ℃, stirred 10 minutes with 1000 rev/mins speed, stirred 180 minutes with 3000 rev/mins speed.Add 4.01 gram acrylic ester polymer tackiness agents (35% MPA solution) afterwards, at room temperature stirred 30 minutes with 3000 rev/mins speed.After removing bead, dispersion liquid is diluted with the MPA of identical weight.Use spin coating device, go up the dispersion liquid that applies gained at glass substrate (Corning 1737-F type), and with 1000 rev/mins speed centrifugal 30 seconds.This layer on hot plate 100 ℃ dry 2 minutes down, again 200 ℃ dry 5 minutes down.The gained bed thickness is 0.4 micron.
The azoic dyestuff (table 1-18) that below is equally applicable to the mass pigmentation plastics can be similar to example I .1 and prepare like that:
Table 1:
R
2＝-NH-(CH
2CH
2)-OH，
-NH-CH
2-CHOH-CH
2-OH，
-NH-(CH
2CH
2)-S-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH
2，
-NH-CH
2-CHOH-CH
2-NH
2，
-NH-CH
2-CON(CH
2CH
2OH)
2，
-NH-CH
2CH
2-CON(CH
2CH
2OH)
2，
Table 2:
R
1＝R
2＝-NH-(CH
2CH
2)-OH，
-NH-CH
2-CHOH-CH
2-OH，
-NH-(CH
2CH
2)-S-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH
2，
-NH-CH
2-CHOH-CH
2-NH
2，
-NH-CH
2-CON(CH
2CH
2OH)
2，
-NH-CH
2CH
2-CON(CH
2CH
2OH)
2，
Table 3:
R
2＝-NH-(CH
2CH
2)-OH，
-NH-CH
2-CHOH-CH
2-OH，
-NH-(CH
2CH
2)-S-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH
2，
-NH-CH
2-CHOH-CH
2-NH
2，
-NH-CH
2-CON(CH
2CH
2OH)
2，
-NH-CH
2CH
2-CON(CH
2CH
2OH)
2，
Table 4:
R
2＝-NH-(CH
2CH
2)-OH，
-NH-CH
2-CHOH-CH
2-OH，
-NH-(CH
2CH
2)-S-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH
2，
-NH-CH
2-CHOH-CH
2-NH
2，
-NH-CH
2-CON(CH
2CH
2OH)
2，
-NH-CH
2CH
2-CON(CH
2CH
2OH)
2，
Table 5:
R
1＝R
2＝-NH-(CH
2CH
2)-OH，
-NH-CH
2-CHOH-CH
2-OH，
-NH-(CH
2CH
2)-S-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH
2，
-NH-CH
2-CHOH-CH
2-NH
2，
-NH-CH
2-CON(CH
2CH
2OH)
2，
-NH-CH
2CH
2-CON(CH
2CH
2OH)
2，
Table 6:
R
2＝-NH-(CH
2CH
2)-OH，
-NH-CH
2-CHOH-CH
2-OH，
-NH-(CH
2CH
2)-S-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH
2，
-NH-CH
2-CHOH-CH
2-NH
2，
-NH-CH
2-CON(CH
2CH
2OH)
2，
-NH-CH
2CH
2-CON(CH
2CH
2OH)
2，
Table 7:
R
2＝-NH-(CH
2CH
2)-OH，
-NH-CH
2-CHOH-CH
2-OH，
-NH-(CH
2CH
2)-S-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH
2，
-NH-CH
2-CHOH-CH
2-NH
2，
-NH-CH
2-CON(CH
2CH
2OH)
2，
-NH-CH
2CH
2-CON(CH
2CH
2OH)
2，
Table 8:
R
1＝R
2＝-NH-(CH
2CH
2)-OH，
-NH-CH
2-CHOH-CH
2-OH，
-NH-(CH
2CH
2)-S-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH
2，
-NH-CH
2-CHOH-CH
2-NH
2，
-NH-CH
2-CON(CH
2CH
2OH)
2，
-NH-CH
2CH
2-CON(CH
2CH
2OH)
2，
Table 9:
R
2＝-NH-(CH
2CH
2)-OH，
-NH-CH
2-CHOH-CH
2-OH，
-NH-(CH
2CH
2)-S-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH
2，
-NH-CH
2-CHOH-CH
2-NH
2，
-NH-CH
2-CON(CH
2CH
2OH)
2，
-NH-CH
2CH
2-CON(CH
2CH
2OH)
2，
Table 10:
R
2＝-NH-(CH
2CH
2)-OH，
-NH-CH
2-CHOH-CH
2-OH，
-NH-(CH
2CH
2)-S-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH
2，
-NH-CH
2-CHOH-CH
2-NH
2，
-NH-CH
2-CON(CH
2CH
2OH)
2，
-NH-CH
2CH
2-CON(CH
2CH
2OH)
2，
Table 11:
R
1＝R
2＝-NH-(CH
2CH
2)-OH，
-NH-CH
2-CHOH-CH
2-OH，
-NH-(CH
2CH
2)-S-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH
2，
-NH-CH
2-CHOH-CH
2-NH
2，
-NH-CH
2-CON(CH
2CH
2OH)
2，
-NH-CH
2CH
2-CON(CH
2CH
2OH)
2，
Table 12:
R
2＝-NH-(CH
2CH
2)-OH，
-NH-CH
2-CHOH-CH
2-OH，
-NH-(CH
2CH
2)-S-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH
2，
-NH-CH
2-CHOH-CH
2-NH
2，
-NH-CH
2-CON(CH
2CH
2OH)
2，
-NH-CH
2CH
2-CON(CH
2CH
2OH)
2，
Table 13:
R
2＝-NH-(CH
2CH
2)-OH，
-NH-CH
2-CHOH-CH
2-OH，
-NH-(CH
2CH
2)-S-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH
2，
-NH-CH
2-CHOH-CH
2-NH
2，
-NH-CH
2-CON(CH
2CH
2OH)
2，
-NH-CH
2CH
2-CON(CH
2CH
2OH)
2，
Table 14:
R
1＝R
2＝-NH-(CH
2CH
2)-OH，
-NH-CH
2-CHOH-CH
2-OH，
-NH-(CH
2CH
2)-S-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH
2，
-NH-CH
2-CHOH-CH
2-NH
2，
-NH-CH
2-CON(CH
2CH
2OH)
2，
-NH-CH
2CH
2-CON(CH
2CH
2OH)
2，
Table 15:
R
2＝-NH-(CH
2CH
2)-OH，
-NH-CH
2-CHOH-CH
2-OH，
-NH-(CH
2CH
2)-S-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH
2，
-NH-CH
2-CHOH-CH
2-NH
2，
-NH-CH
2-CON(CH
2CH
2OH)
2，
-NH-CH
2CH
2-CON(CH
2CH
2OH)
2，
Table 16:
R
2＝-NH-(CH
2CH
2)-OH，
-NH-CH
2-CHOH-CH
2-OH，
-NH-(CH
2CH
2)-S-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH
2，
-NH-CH
2-CHOH-CH
2-NH
2，
-NH-CH
2-CON(CH
2CH
2OH)
2，
-NH-CH
2CH
2-CON(CH
2CH
2OH)
2，
Table 17:
R
1＝R
2＝-NH-(CH
2CH
2)-OH，
-NH-CH
2-CHOH-CH
2-OH，
-NH-(CH
2CH
2)-S-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH
2，
-NH-CH
2-CHOH-CH
2-NH
2，
-NH-CH
2-CON(CH
2CH
2OH)
2，
-NH-CH
2CH
2-CON(CH
2CH
2OH)
2，
Table 18:
R
2＝-NH-(CH
2CH
2)-OH，
-NH-CH
2-CHOH-CH
2-OH，
-NH-(CH
2CH
2)-S-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH-(CH
2CH
2)-OH，
-NH-(CH
2CH
2)-NH
2，
-NH-CH
2-CHOH-CH
2-NH
2，
-NH-CH
2-CON(CH
2CH
2OH)
2，
-NH-CH
2CH
2-CON(CH
2CH
2OH)
2，
Claims (11)
1. the azoic dyestuff of formula (I):
Wherein:
R
1And R
2Be independently of one another separately-NH-(CH
2CH
2)-OH ,-NH-CH
2-CHOH-CH
2-OH ,-NH-(CH
2CH
2)-S-(CH
2CH
2)-OH ,-NH-(CH
2CH
2)-NH-(CH
2CH
2)-OH ,-NH-(CH
2CH
2)-NH
2,-NH-CH
2-CHOH-CH
2-NH
2,-NH-CH
2-CON (CH
2CH
2OH)
2,-NH-CH
2CH
2-CON (CH
2CH
2OH)
2,
Or
R
3Be-CN or-CONH
2,
R
4Be methyl or trifluoromethyl,
R
5Be-CF
3,-COOC
2H
5,
R
6Be hydrogen or chlorine and
R
7Be hydrogen, chlorine, bromine or-NO
2
2. according to the azoic dyestuff of claim 1, R wherein
3Be-CN R
4It is methyl.
3. according to the azoic dyestuff of claim 1 or 2, R wherein
1And R
2Be-NH-(CH
2CH
2)-OH or
4. according at each azoic dyestuff of aforementioned claim, wherein R
7Be hydrogen.
5. formula (Ia), (Ib), (Ic) or azoic dyestuff (Id):
6. prepare the method for the described formula of claim 1 (I) azoic dyestuff, it comprises: according to the method for the routine compound diazotization with formula (II):
Wherein, R
5, R
6And R
7Definition is with claim 1, and then makes the coupling component coupling of this diazotizing compound and formula (III):
Wherein, R
1, R
2, R
3And R
4Definition is with claim 1.
7. make the method for mass pigmentation plastics or polymkeric substance pigment particle, it comprises high molecular weight organic materials is mixed with the described formula of at least a claim 1 (I) azoic dyestuff of painted significant quantity.
8. make the method for mass pigmentation plastics or polymkeric substance pigment particle, it comprises making and comprises that at least a monomeric mixture that includes at least one NH-, OH-or SH-active group and can carry out polymerization, addition polymerization or polycondensation reacts with the described formula of at least a claim 1 (I) compound.
9. each the purposes of azoic dyestuff in making mass pigmentation plastics or polymkeric substance pigment particle of claim 1-5.
10. according to claim 7 or painted plastics or the polymkeric substance pigment particle of 8 described methods.
11. the described azoic dyestuff of claim 1 is as the purposes of tinting material in producing colour filter.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02405224.3 | 2002-03-22 | ||
| EP02405224 | 2002-03-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1643077A true CN1643077A (en) | 2005-07-20 |
Family
ID=28051878
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA038066084A Pending CN1643077A (en) | 2002-03-22 | 2003-03-13 | Azo dyes |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7026459B2 (en) |
| EP (1) | EP1487922B1 (en) |
| JP (1) | JP2005520908A (en) |
| KR (1) | KR101017849B1 (en) |
| CN (1) | CN1643077A (en) |
| AT (1) | ATE544822T1 (en) |
| AU (1) | AU2003219050A1 (en) |
| BR (1) | BRPI0308598B1 (en) |
| CA (1) | CA2476591C (en) |
| MX (1) | MXPA04008193A (en) |
| RU (1) | RU2324714C2 (en) |
| TW (1) | TWI261062B (en) |
| WO (1) | WO2003080737A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103270452A (en) * | 2010-12-29 | 2013-08-28 | 第一毛织株式会社 | Photosensitive resin composition for color filter and color filter using same |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1572808A1 (en) * | 2002-12-19 | 2005-09-14 | Ciba SC Holding AG | Phthalimidylazo dyes, processes for the preparation thereof and the use thereof |
| WO2006024618A1 (en) * | 2004-09-03 | 2006-03-09 | Huntsman Advanced Materials (Switzerland) Gmbh | Cyanopyridine-based azo dyes |
| GB0521549D0 (en) * | 2005-10-22 | 2005-11-30 | Avecia Inkjet Ltd | Yellow azo dyes for ink jet printing |
| KR20140076320A (en) | 2012-12-12 | 2014-06-20 | 제일모직주식회사 | Photosensitive resin composition and black spacer using the same |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4712585Y1 (en) * | 1967-02-22 | 1972-05-10 | ||
| NL7117139A (en) * | 1970-12-19 | 1972-06-21 | Basf Ag | |
| US3998802A (en) * | 1970-12-19 | 1976-12-21 | Basf Aktiengesellschaft | Azo dye with a 3-cyano- or 3-carbamoyl-4-methyl-2,6-diamino-pyridine coupling component |
| DE2263458A1 (en) | 1972-12-27 | 1974-07-04 | Basf Ag | 2,6-DIAMINOPYRIDINE DYES |
| CH596263A5 (en) * | 1972-03-10 | 1978-03-15 | Basf Ag | |
| IT985617B (en) * | 1972-04-06 | 1974-12-10 | Basf Ag | WATER-SOLUBLE AZO-DYES OF THE 2 6 DIAMMINOPYRIDINE SERIES |
| DE2222873A1 (en) * | 1972-05-10 | 1973-11-22 | Basf Ag | Dispersion dyeing polyesters - using 2,6-diamino-3-azo-pyridyl dye in perchloroethylene |
| JPS497419A (en) * | 1972-05-24 | 1974-01-23 | ||
| US3974123A (en) * | 1974-03-01 | 1976-08-10 | Basf Aktiengesellschaft | Dyes for thermoplastics |
| DE2930919A1 (en) * | 1979-07-30 | 1981-02-26 | Basf Ag | METHOD FOR COLORING AND PRINTING CELLULOSE-CONTAINING TEXTILE MATERIAL |
| DE3021294A1 (en) * | 1980-06-06 | 1981-12-24 | Basf Ag, 6700 Ludwigshafen | METHOD FOR COLORING COATING MASKS, ORGANIC SOLVENTS AND MINERAL OIL PRODUCTS, AND NEW DYES |
| JP2002014223A (en) * | 2000-06-30 | 2002-01-18 | Sumitomo Chem Co Ltd | Color filter array having yellow filter layer and method for manufacturing the same |
| DE60223000T2 (en) | 2001-01-26 | 2008-07-24 | Huntsman Advanced Materials (Switzerland) Gmbh | AZO DYES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE IN THE PRODUCTION OF COLORED PLASTICS OR POLYMERIC COLOR PARTICLES AND IN THE COLORING OR PRINTING OF HYDROPHOBIC FIBER MATERIALS |
| WO2002059216A1 (en) | 2001-01-26 | 2002-08-01 | Ciba Specialty Chemicals Holding Inc. | Azo dyes, a process for their preparation and their use in the dyeing or printing of hydrophobic fibre materials |
-
2003
- 2003-03-13 RU RU2004131536/04A patent/RU2324714C2/en not_active IP Right Cessation
- 2003-03-13 US US10/508,713 patent/US7026459B2/en not_active Expired - Fee Related
- 2003-03-13 JP JP2003578475A patent/JP2005520908A/en active Pending
- 2003-03-13 AU AU2003219050A patent/AU2003219050A1/en not_active Abandoned
- 2003-03-13 MX MXPA04008193A patent/MXPA04008193A/en active IP Right Grant
- 2003-03-13 EP EP03714819A patent/EP1487922B1/en not_active Expired - Lifetime
- 2003-03-13 CN CNA038066084A patent/CN1643077A/en active Pending
- 2003-03-13 BR BRPI0308598A patent/BRPI0308598B1/en not_active IP Right Cessation
- 2003-03-13 CA CA2476591A patent/CA2476591C/en not_active Expired - Fee Related
- 2003-03-13 AT AT03714819T patent/ATE544822T1/en active
- 2003-03-13 KR KR1020047014835A patent/KR101017849B1/en not_active IP Right Cessation
- 2003-03-13 WO PCT/EP2003/002614 patent/WO2003080737A1/en active Application Filing
- 2003-03-20 TW TW092106152A patent/TWI261062B/en not_active IP Right Cessation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103270452A (en) * | 2010-12-29 | 2013-08-28 | 第一毛织株式会社 | Photosensitive resin composition for color filter and color filter using same |
| US8961837B2 (en) | 2010-12-29 | 2015-02-24 | Cheil Industries Inc. | Photosensitive resin composition for color filter and color filter using same |
| CN103270452B (en) * | 2010-12-29 | 2016-09-28 | 第一毛织株式会社 | For the photosensitive resin composition of colored filter and the colored filter using it |
Also Published As
| Publication number | Publication date |
|---|---|
| TW200306333A (en) | 2003-11-16 |
| KR20040097192A (en) | 2004-11-17 |
| TWI261062B (en) | 2006-09-01 |
| WO2003080737A1 (en) | 2003-10-02 |
| EP1487922B1 (en) | 2012-02-08 |
| US20050176857A1 (en) | 2005-08-11 |
| BR0308598A (en) | 2005-02-09 |
| ATE544822T1 (en) | 2012-02-15 |
| CA2476591A1 (en) | 2003-10-02 |
| MXPA04008193A (en) | 2004-11-26 |
| CA2476591C (en) | 2011-02-08 |
| BRPI0308598B1 (en) | 2015-12-01 |
| US7026459B2 (en) | 2006-04-11 |
| RU2324714C2 (en) | 2008-05-20 |
| JP2005520908A (en) | 2005-07-14 |
| EP1487922A1 (en) | 2004-12-22 |
| AU2003219050A1 (en) | 2003-10-08 |
| RU2004131536A (en) | 2005-09-20 |
| KR101017849B1 (en) | 2011-03-04 |
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